Triethylamine → HCID 58762507, compound

HRID 858867Notes

Reaction equation

Cl[CH:2]1[C:7](=[O:8])[CH2:6][C:5]([CH:20]2[CH2:24][CH2:23][CH2:22][CH2:21]2)([CH2:9][CH2:10][C:11]#[C:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([OH:19])[CH:14]=2)[O:4][C:3]1=[O:25].[SH:26][C:27]1[S:28][CH:29]=[CH:30][N:31]=1.C(N(CC)CC)C>CN(C=O)C>[CH:20]1([C:5]2([CH2:9][CH2:10][C:11]#[C:12][C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([OH:19])[CH:14]=3)[O:4][C:3](=[O:25])[C:2]([S:26][C:27]3[S:28][CH:29]=[CH:30][N:31]=3)=[C:7]([OH:8])[CH2:6]2)[CH2:24][CH2:23][CH2:22][CH2:21]1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 3-chloro-6-cyclopentyl-6-[4-(3-hydroxy-phenyl)-but-3-ynyl]-dihydro-pyran-2,4-dione (216 mg, 0.6 mmol) from Step 5 below and 2-mercaptothiazole (141 mg, 1.2 mmol) in DMF (6 mL) was added triethylamine (0.15 mL, 1.2 mmol). The reaction was stirred at 50° C. for 2.5 hours and then quenched with 10 mL of saturated ammonium chloride. The mixture was further acidified to a pH of 1–2 with 1 N HCl. To this mixture was added 10 mL CH2Cl2 and the layers were separated. The aqueous was extracted with 2×10 mL CH2Cl2, and the organic layers were combined. After drying the organic layer over MgSO4, the solids were filtered away and the liquid was concentrated to an oil. The oil was chromatographed on silica to yield the desired product (28 mg, 11% yield).

Workup

customquenched with 10 mL of saturated ammonium chloride
additionTo this mixture was added 10 mL CH2Cl2
customthe layers were separated
extractionThe aqueous was extracted with 2×10 mL CH2Cl2
dry with materialAfter drying the organic layer over MgSO4
filtrationthe solids were filtered away
concentrationthe liquid was concentrated to an oil
customThe oil was chromatographed on silica

Sources & evidence

ORD record: ord-111b18dbb32049d68cd2ed1b78e104a8
Source dataset: uspto-grants-2006_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07148226B2

Reaction notes

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